Method for producing thiocarbamate derivative

Abstract

An O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamate represented by the following formula (I): (wherein R 1 , R 2 and Ar are as defined below) is produced by treating a phenol represented by the following general formula (IV): Ar—OH  (IV) (wherein Ar represents an aryl group) with a base in a solvent and then adding thereto an alkali metal salt of N-(6-alkoxy-2-pyridyl)-N-alkyldithiocarbamic acid represented by the following general formula (III): (wherein R 1 and R 2 independently represent a C 1 -C 4 alkyl group and M represents an alkali metal) and a halomethane represented by the following general formula (V): CH 2 X m Y n   (V) (wherein X and Y represent different halogen atoms, m represents 0, 1 or 2, n represents 0, 1 or 2, and m+n equals 2) for causing a reaction.

1. A method of producing an O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamate represented by formula (I): 
       
         
           
           
               
               
           
         
         (wherein R 1  and R 2 , independent of each other, denote C 1 -C 4  alkyl groups and Ar denotes an aryl group), comprising treating a phenol represented by formula (IV):
   Ar—OH  (IV) 
 
         (wherein Ar is as defined above) with a base in a solvent, adding thereto an alkali metal salt of N-(6-alkoxy-2-pyridyl)-N-alkyldithiocarbamic acid represented by formula (III): 
       
       
         
           
           
               
               
           
         
         (wherein R 1  and R 2  are as defined above, and M denotes an alkali metal) and a halomethane represented by formula (V):
   CH 2 X m Y n   (V) 
 
         (wherein X and Y denote different halogen atoms, m denotes 0, 1 or 2, n denotes 0, 1 or 2, and m+n=2), and allowing to react to produce said O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamate represented by formula (I). 
       
     
     
       2. A method of producing an O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamate represented by formula (I): 
       
         
           
           
               
               
           
         
         (wherein R 1  and R 2 , independent of each other, denote C 1 -C 4  alkyl groups and Ar denotes an aryl group), comprising: 
         causing a 6-alkoxy-2-alkylaminopyridine represented by formula (II): 
       
       
         
           
           
               
               
           
         
         (wherein R 1  and R 2  are as defined above) to react with carbon disulfide in the presence of a base, to produce an alkali metal salt of N-(6-alkoxy-2-pyridyl)-N-alkyldithiocarbamic acid represented by formula (III): 
       
       
         
           
           
               
               
           
         
         (wherein R 1  and R 2  are as defined above, and M denotes an alkali metal); and 
         treating a phenol represented by formula (IV):
   Ar—OH  (IV) 
 
         (wherein Ar is as defined above) with a base in a solvent, adding thereto said alkali metal salt of N-(6-alkoxy-2-pyridyl)-N-alkyldithiocarbamic acid represented by formula (III) and a halomethane represented by formula (V):
   CH 2 X m Y n   (V) 
 
         (wherein X and Y denote different halogen atoms, m denotes 0, 1 or 2, n denotes 0, 1 or 2, and m+n=2), and allowing to react to produce said O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamate represented by formula (I). 
       
     
     
       3. A method in accordance with  claim 1  or  2 , wherein R 1  and R 2  are both methyl groups. 
     
     
       4. A method in accordance with  claim 1  or  2 , wherein Ar is a tetrahydronaphthyl group, or a phenyl group optionally substituted by a C 1 -C 4  alkyl group. 
     
     
       5. A method in accordance with  claim 1  or  2 , wherein M is sodium. 
     
     
       6. A method in accordance with  claim 1  or  claim 2 , wherein the halomethane of formula (V) is CH 2 Cl 2 , CH 2 Br 2 , CH 2 I 2  or CH 2 BrCl. 
     
     
       7. A method in accordance with  claim 2 , wherein the base in step A is sodium hydride. 
     
     
       8. A method in accordance with  claim 1  or  claim 2 , wherein the solvent used in the reaction from the alkali metal salt of dithiocarbamic acid represented by formula (III) to the compound represented by formula (I) is N,N-dimethylformamide.